Yes, the first million is the hardest. Even though he was a buy and hold investor before making millions in business, those millions probably made it a lot easier to buy/hold. At least it does for most people. The reason is that you already have "enough" and are not so afraid to lose some on a bet here or there. And that's why I advise people to disassociate from their money and to not think of stocks as being money. And to figure out how to live fulfilling lives without spending a lot.
What you're pointing out here is the heart of the disagreement we had a few days back, and I feel it's a point that's worth emphasizing further. Money has different "utility values" at different points in life, and this is also affected by personal preferences. For someone who e.g. considers most paid work a chore and a necessary evil, or has a family, it might be a rational choice to e.g. sell (parts of) an expected winner for diversification to other income-generating assets, leading to a very high likelihood of having complete freedom over one's time and career choices forever. In this situation, reducing the risk of a big (even temporary) drawdown might outweigh a higher expected return.
While, as you point out, reaching a position of complete economic independence is likely to make it much easier to make investment decisions that are purely expected to yield the highest returns. Such investments will usually have a volatility that's hard to stomach if one's personal situation means a couple of $100k is a life-changing amount of money. I think this is big part of the reason why we see so many compounding fortunes after the $1 million mark. The people capable of disassociating from volatility and risk without a heavy wealth cushion are a rare breed, so for most it takes extreme focus to keep cool in that situation. With a million or two in the bank....meh, who cares. You can do almost whatever you want regardless of what happens. Feelings are dampened, leading to investment decisions that are driven by expected return to a much greater degree.
Selling big part of a winning stock with future potential for something non-compounding like a remodel or a car is rarely a sound choice IMHO. Diversification to a different income-generating asset could be, in the situation outlined above. In that case, it's probably healthy to be aware that one might give up a fortune that's multiples higher, and make a considered choice. Happy & safe regardless of money situation? Go for it.
Everyone wishes they'd bought bitcoin at $.5. Almost no working person would have held to >$1000, or even close. A rare few would have kept a double-digit percentage to $17k and back down to a few thousand. Whereas capital class people will find it much easier to make cold decisions.
Edit:
A need to constantly spend money makes money seem scarce and that is not a winning mindset. You want a mindset that you already have more than you need.
Perfectly agree with this. Of course, the most effective way to enter this mindset is to
actually have more than you need already
From what I see on this forum, we probably have a fair amount of members that are capable of disassociating investment returns from strong emotional reactions. But this is actually a very rare trait, especially when combined with a life that's healthy in all other ways, and the frequency of this type of people shows that this is a quite rare online community.